Route 66 Road Trip: From Chicago Through America’s Heartland

Next, roll into Wilmington and pay a visit to Gemini Giant, a 30-foot Muffler Man, before continuing on to Pontiac. There, the Route 66 Hall of Fame & Museum offers enough nostalgia to fill a ’57 Chevy.

Allow time for a stop by the Towanda Route 66 roadside attraction to learn even more Route 66 history before finishing your day in Bloomington-Normal. For a modern brewpub experience, grab a table at Destihl, or tuck into classic roadside diner fare at Portillo’s.

The first pull-off will be the Dixie Truck Stop in Mclean, which has changed official names a few times over the years but nonetheless is where truckers have been swapping tales since 1928. Then ramble on towards Lincoln, where the world’s largest covered wagon makes the pioneer-perfect backdrop for your socials. Also in Lincoln is the Lincoln Heritage Museum at Lincoln College, celebrating the life and works of America’s 16th president. By late afternoon, you’ll reach Springfield, Illinois, where history meets hospitality in charming bed and breakfasts like the Audrey, the Bressmer, and the Inn at 365.

Before crossing the mighty Mississippi River, salute the World’s Largest Catsup Bottle in Collinsville and explore the ancient Cahokia Mounds State Historic Site. A UNESCO World Heritage Site and the largest pre-Columbian site north of Mexico, the area was once home to a civilization of over 20,000 inhabitants. 

Finally, cross the Chain of Rocks Bridge into Missouri and take caution on the 22-degree bend in the road, which causes even the most well-seasoned drivers to white-knuckle.

Another can’t-miss is the National Museum of Transportation, which ushers visitors through decades of transportation technology and development. Meanwhile, barbecue enthusiasts can sample platefuls of some of America’s most iconic cuisine of smoked meats and sauces.

When you’re ready head on, follow the trail of barn advertisements onward to Cuba, Missouri. The “Mural City” is speckled with larger-than-life public art, and also home to the Wagon Wheel Motel. You’ll sleep tight here at the oldest continuously operated motel on Route 66 where the neon sign has been glowing since Harry Truman was president!

Optional Add-On: Mark Twain National Forest

You’ll need to budget a bit more time for this detour, but it’s well-worth your while to explore over 750 miles of hiking, biking, horseback riding, and all-terrain vehicle trails.

The last day of our Route 66 Heartland itinerary takes us to Lebanon’s Route 66 Museum endearingly located in the public library. Then crawl (not literally!) through Springfield’s Fantastic Caverns – America’s only ride-through cave system where specialized vehicles guide visitors through the extensive cave system. As you cruise down Route 66 towards the Kansas border, stop off at Grand Falls near Joplin which includes several swimming spots.

The last major stop of the day is just across the Kansas state line in the small municipality of Galena. There, Cars on the Route, a lovely homage to the Disney Pixar move “Cars,” is a delightful finale for road trippers of all ages.

End your journey in Baxter Springs, Kansas, where there are plenty of Route 66 road signs to snap a photo in front of. If your wallet’s feeling a bit light by this point in the trip, the Baxter Springs campground has affordable accommodation for many a weary traveler.

Optional Add-On: Ozark National Forest

Regardless of whether you’re a fan of the hit Netflix series, you’re sure to be a fan of the stunning landscapes found in Ozark-St. Francis National Forest. This excursion will take you down to northwest Arkansas, well off the Route 66 path, but it’s worth the extra detour if you have time!